CN105622406B - 功能化柱[5]芳烃三聚体的制备方法和应用 - Google Patents
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Abstract
本发明公开了功能化柱[5]芳烃三聚体的制备方法和应用。该柱[5]芳烃三聚体类化合物在主客体作用中具有良好的协同作用,功能化柱[5]芳烃三聚体的制备方法是采用化学合成方法,以对甲氧基苯与多聚甲醛为起始原料,通过催化、合成反应得到产品。本产品原料简单易得、方法操作简单,反应条件温和。对直链型二胺盐酸盐和支链型三胺盐酸盐两类阳离子分子识别中,能发生明显的电荷转移,在紫外上体现出非常特征的吸收峰,可用于紫外检测。
Description
技术领域
本发明涉及一种功能化柱[5]芳烃三聚体,具体是功能化柱[5]芳烃三聚体的制备方法和应用。
技术背景
随着柱[5]芳烃的研究发展,大量关于其上下缘结构修饰的衍生物及主客体化学被报道。然而,关于柱[5]芳烃多聚体的研究报道仍较为少见,我们已经知道柱[5]芳烃二聚体在络合能力要优于单聚体的络合能力,而且更加稳定,具有诱惑力。三聚体以及四聚体与相宜客体可以形成网状或立体状聚合物,在纳米材料、荧光材料等领域具有潜在用途。即使如此,基于柱芳烃多聚体间的协同作用研究还较为鲜见。为此,我们将1,3,5-均三苯甲酰基团引入到柱[5]芳烃体系成功合成了1,3,5-均三苯甲酰基团桥连柱[5]芳烃三聚体1。通过紫外光谱滴定法测定该化合物与1,4-丁二胺双盐酸盐BDA-HCl和三(2-氨基乙基)胺四盐酸盐TA-HCl的络合选择性,结果显示,超分子1与客体BDA-HCl和TA-HCl具有良好的协同作用,适用于紫外检测。
发明内容
本发明的目的是提供功能化柱[5]芳烃三聚体的制备方法和应用。本发明产品原料廉价易得,方法操作简单,反应条件温和。
本发明解决上述技术问题的技术方案如下:
本发明的目的是:采用化学合成方法,制备一种新型的酯类柱[5]芳烃三聚体,其结构式如(I),研究该柱[5]芳烃三聚体类化合物与直链型二胺盐酸盐和支链型三胺盐酸盐两类阳离子分子的协同作用和识别应用,开拓柱[5]芳烃主客体化学的研究,为上述两类铵盐客体分子的识别寻找一种可行的检测方法。
1.一种功能化柱[5]芳烃三聚体化合物具有如下(I)的结构通式:
2.功能化柱[5]芳烃三聚体化合物的制备方法,通过如下反应制得:
所述的反应步骤如下:
第一步,在氮气保护下,以对甲氧基苯与多聚甲醛摩尔比1:3为原料,三氯化铁为催化剂,二氯甲烷为溶剂,在25~30℃下生成1,4-二甲氧基柱[5]芳烃。
第二步,在0~-8℃条件下干燥三氯甲烷为溶剂,在1,4-二甲氧基柱[5]芳烃中加入1-5倍摩尔量三溴化硼,生成单羟基甲基柱[5]芳烃。
第三步,在氮气保护下,单羟基甲基柱[5]芳烃溶于干燥的三氯甲烷中,与1,3,5-均三苯甲酰氯在70℃下,以三乙胺为缚酸剂搅拌4小时,生成化合物I-功能化柱[5]芳烃三聚体化合物。
3.功能化柱[5]芳烃三聚体化合物作为铵盐阳离子识别受体的应用。所述铵盐阳离子为直链型二铵盐或支链型三铵盐。
本发明所述I化合物紫外中选择性络合作用的盐可通过以下反应合成:
上述所述的主客体络合选择性的试验是采用紫外光谱滴定法测试柱[5]芳烃三聚体I对1,4-丁二胺双盐酸盐BDA-HCl和三(2-氨基乙基)胺四盐酸盐TA-HCl的络合选择性。结果表明,P5T与客体BDA-HCl和TA-HCl具有良好的协同作用和识别作用。
附图说明
图1柱[5]芳烃三聚体与1,4-丁二胺双盐酸盐紫外光谱测试结果。
图2柱[5]芳烃三聚体与三(2-氨基乙基)胺四盐酸盐紫外光谱测试结果。
具体实施方式
下面结合实施例对本发明作进一步的说明,需要说明的是,下述实施例仅是用于说明,而并非限制本发明。本领域技术人员根据本发明的教导所做出的各种变化均应在本申请权利要求所要求的保护范围之内。
实施例1
功能化柱[5]芳烃三聚体的制备方法:
在氮气保护下,向500mL两口烧瓶中依次加入1.65g(12.0mmol)1,4-二甲氧基苯、1.08g(36mmol)多聚甲醛、300mL干燥的二氯甲烷,搅拌均匀后加入0.31g(1.92mmol)无水三氯化铁,25~30℃条件下,继续反应2~3小时,TLC跟踪,反应结束后,往体系中加入150mL去离子水终止反应。然后,滤去残渣,收集有机层,用二氯甲烷萃取(50mL×3),合并有机层,无水硫酸钠干燥过夜,柱层析分离得到1.25g白色固体1,4-二甲氧基柱[5]芳烃。以对甲氧基苯与多聚甲醛的摩尔比1:3为原料,三氯化铁为催化剂,二氯甲烷为溶剂,在25-30℃下生成1,4-二甲氧基柱[5]芳烃;在氮气保护下,向250mL两口烧瓶中依次加入490mg(0.65mmol)1,4-二甲氧基柱[5]芳烃,98mL重蒸新制的三氯甲烷,加入3A分子筛干燥剂,搅拌充分,在0~-8℃条件下,准确加入242μL(2.60mmol)BBr3,反应1.5h后,加入100mL 去离子水终止反应,静置过滤,收集有机层,然后,三氯甲烷萃取(50mL×3),合并有机相,无水硫酸钠干燥过夜,柱层析分离纯化得到265mg白色固体单羟基甲基柱[5]芳烃;在氮气保护下,向25mL的两口烧瓶中,依次加入10mL三氯甲烷、30mg(0.11mmol)1,3,5-均三苯甲酰氯、1mL三乙胺搅拌均匀,缓慢滴加300mg(0.41mmol)2的三氯甲烷溶液,在回流条件下,反应4小时,以TLC跟踪反应(展开剂为V乙酸乙酯:V石油醚=1:2),反应结束后,冷却至室温,将反应液倒入20mL去离子水,二氯甲烷萃取(10mL×3),合并有机层,用无水硫酸钠干燥,用中低压制备色谱柱梯度洗脱,洗脱剂为V乙酸乙酯:V石油醚=1:20增加到1:2,得到化合物I-功能化柱[5]芳烃三聚体化合物。
上述实施例中,为了此柱[5]芳烃三聚体化合物的结构进行确证,本发明人对红外、氢谱、碳谱、质谱进行解析,确证了其结构化合物表征数据见表1。
表1功能化柱[5]芳烃三聚体的结构及波谱数据
实施例2
功能化柱[5]芳烃三聚体的主客体络合选择性实验:
在紫外光谱仪的样品池中,以氯仿/甲醇(v/v=9:1)为测试溶剂:
1.测试DBA-HCl溶液6×10-4mol L-1浓度的吸收曲线;
2.测试柱[5]芳烃三聚体主体浓度为1×10-4mol·L-1的吸收曲线,然后向体系中逐渐加入客体DBA-HCl,结果如图1(A)所示。
3.测试客体TA-HCl在6×10-4mol L-1浓度的吸收曲线。
4.测试柱[5]芳烃三聚体主体浓度为1×10-4mol·L-1的吸收曲线,然后向体系中逐渐加入客体TA-HCl,结果如图2(A)所示。
图1(A)是功能化柱[5]芳烃三聚体1加入客体DB-HCl的紫外光谱滴定变化图,固定主体1的浓度为1×10-4mol·L-1,向体系中逐渐加入客体DB-HCl,出现了显著的电子转移吸收带,这说明客体与主体形成了配合物,随着G/H的增大,电子转移吸收带吸收明显增强。如图1(B)所示,以428nm处的吸光度变化为例,当G/H约等于2.5时,吸光度发生明显的突变,直至G/H约等于3.0变化增加值开始减小。
图2(A)是主体1体系中逐渐加入客体TA-HCl的紫外光谱滴定变化图,从图中可知主客体间形成了配合物,随着配合物的浓度增加,吸光度呈现了明显的增大趋势,由图2(B)可知,当G/H约等于1.2时,吸光度发生明显的突变,至G/H约等于2.5时变化增加值开始减小。
实验结果表明,功能化柱[5]芳烃三聚体与客体1,4-丁二胺双盐酸盐BDA-HCl和三(2-氨基乙基)胺四盐酸盐TA-HCl在氯仿/甲醇(v/v=9:1)溶剂中形成了稳定的复合物,产生了电子转移带,说明功能化柱[5]芳烃三聚体与客体BDA-HCl和TA-HCl具有良好的协同作用和识别作用,适应于紫外识别检测。
Claims (3)
1.一种功能化柱[5]芳烃三聚体化合物,其特征在于:具有如下(I)的结构通式:
2.如权利要求1所述的功能化柱[5]芳烃三聚体化合物的制备方法,其特征在于:通过如下反应制得:
所述的反应步骤如下:
第一步,在氮气保护下,以对苯二甲醚与多聚甲醛摩尔比1:3为原料,三氯化铁为催化剂,二氯甲烷为溶剂,在25~30℃下生成1,4-二甲氧基柱[5]芳烃;
第二步,在0~-8℃条件下干燥三氯甲烷为溶剂,在1,4-二甲氧基柱[5]芳烃中加入1-5倍摩尔量三溴化硼,生成单羟基甲基柱[5]芳烃;
第三步,在氮气保护下,单羟基甲基柱[5]芳烃溶于干燥的三氯甲烷中,与1,3,5-均三苯甲酰氯在70℃下,以三乙胺为缚酸剂搅拌4小时,生成化合物I-功能化柱[5]芳烃三聚体化合物。
3.如权利要求1所述功能化柱[5]芳烃三聚体化合物的应用,其特征在于:该化合物作为铵盐阳离子识别受体的应用,所述铵盐阳离子为直链型1,4-丁二胺双盐酸盐铵盐阳离子和支链型三(2-氨基乙基)胺四盐酸盐铵盐阳离子。
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